Oakland Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Oakland Vacation
From its cycling to its walking, there's tons to love about Oakland. Book a customized Oakland vacation package and get ready to fall for the delights of this neighborhood. When it's time to head out and explore, you'll find lots of big-name attractions nearby including Acrisure Stadium, University of Pittsburgh and PNC Park. Tick off one, two or all during your trip to Oakland. No matter your travel plans or budget, booking the ultimate Oakland vacation is simple with Expedia.
Price found within the past 48 hours. Click for updated prices.
- Crowne Plaza Suites Pittsburgh South by IHG
Jul 7 - Jul 13Crowne Plaza Suites Pittsburgh South by IHG + Flight
Bethel Park6 nights8.8/10 - Excellent (1,004 reviews)"Staff nice"Reviewed May 15, 2026Roundtrip • Boston (BOS) - Pittsburgh (PIT)BOS - PIT • Nonstop PIT - BOS • Nonstop$721$554found 1 day agoper traveler - Stay Pittsburgh
Jul 7 - Jul 13Stay Pittsburgh + Flight
Downtown Pittsburgh6 nights8.0/10 - Very Good (282 reviews)"It is spacious rooms with dining and living room with nice couches. It is in downtown Pittsburg but quite at night. I liked very much and will visit again in the future"Reviewed May 16, 2026Roundtrip • Boston (BOS) - Pittsburgh (PIT)BOS - PIT • Nonstop PIT - BOS • Nonstop - Holiday Inn Express & Suites Pittsburgh North Shore by IHG
Jul 7 - Jul 13Holiday Inn Express & Suites Pittsburgh North Shore by IHG + Flight
North Shore6 nights8.6/10 - Excellent (1,416 reviews)"Staff was friendly. Easy to get to location."Reviewed May 18, 2026Roundtrip • Boston (BOS) - Pittsburgh (PIT)BOS - PIT • Nonstop PIT - BOS • Nonstop$926$749found 1 day agoper traveler - DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown
Jul 7 - Jul 13DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown + Flight
Downtown Pittsburgh6 nights8.2/10 - Very Good (1,060 reviews)"Parking was terrible! No parking on site. They do offer shady valet parking. I refused to do valet parking based on how the works sped off in other people’s cars. Required underground parking deck parking. Not easily accessible to hotel. Which you were also changed for parking and no voucher received."Reviewed May 17, 2026Roundtrip • Boston (BOS) - Pittsburgh (PIT)BOS - PIT • Nonstop PIT - BOS • Nonstop$861$706found 1 day agoper traveler - The Maverick by Kasa
Jul 7 - Jul 13The Maverick by Kasa + Flight
East Liberty6 nights9.0/10 - Wonderful (969 reviews)"I love this hotel! My room was fantastic and clean. The bar downstairs is great with beautiful decor. I loved the neighborhood too. My only complaint was not having a cart for my luggage or a ramp for my rolling luggage. No valet or on-site parking; however, there is a public parking lot right next to the hotel. An Uber got me over to the North Shore for a Pirates game within just a few minutes. I would definitely stay here again."Reviewed May 18, 2026Roundtrip • Boston (BOS) - Pittsburgh (PIT)BOS - PIT • Nonstop PIT - BOS • Nonstop$720$598found 1 day agoper traveler
Where to stay in Oakland
Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Downtown Pittsburgh
2 out of top 10 points of interest in this area
4.5/5(2,278 area reviews)
Discover the urban downtown center, home to historic sites like Point State Park and the Cultural District. Enjoy diverse shopping options and easy access to public transportation, including the "T" light rail and bus networks.
Oakland Hotel Deals
Courtyard by Marriott Pittsburgh University Center
100 Lytton Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $148 total per night from May 25 to May 26
$148 total
May 25 - May 26
Total with taxes and fees
Hotel Indigo Pittsburgh University-Oakland by IHG
329 Technology Drive Pittsburgh PA
Fully refundable
$118 nightly
The price is $135 total per night from May 25 to May 26
$135 total
May 25 - May 26
Total with taxes and fees
8.6/10 Excellent! (1,004 reviews)
"Beautiful hotel. Super clean."
Reviewed on May 18, 2026
Residence Inn Pittsburgh Oakland/University Place
3341 Forbes Ave Pittsburgh PA
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $154 total per night from May 21 to May 22
$154 total
May 21 - May 22
Total with taxes and fees
9.2/10 Wonderful! (986 reviews)
"Great breakfast and great location"
Reviewed on May 14, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Discover the most popular places to visit in Oakland
University of Pittsburgh
Enjoy the collegiate vibe around University of Pittsburgh, a top college in Pittsburgh. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.
Carnegie Museum of Natural History
From rare jaguars to geological marvels and ancient fossils, you’ll find it all at this Pittsburgh institution, one of the country’s largest natural history museums.
Soldiers and Sailors Memorial Hall and Museum
You can spend an afternoon browsing the exhibits at Soldiers and Sailors Memorial Hall and Museum during your trip to Pittsburgh. Attend a sporting event or visit the shops in this family-friendly area.
Things to do
Pittsburgh: Museum of Illusions Entrance Ticket
$29
per adult
80% of travellers recommend
Pittsburgh: Beauty of the Burgh Bike Tour
$59
per adult
94% of travellers recommend
Explore a world of travel with Expedia
- Pittsburgh Hotels
- Hotels near Downtown Pittsburgh
- Hotels near University of Pittsburgh
- Hotels near University of Pittsburgh Medical Center
- Hotels near Petersen Events Center
- Hotels near Soldiers and Sailors Memorial Hall and Museum
- Hotels near Cathedral of Learning
- Hotels near Heinz Memorial Chapel
- Hotels near Carnegie Library of Pittsburgh
- Hotels near North Oakland
- Hotels near Carnegie Museum of Natural History
- Hotels near Pittsburgh Playhouse
- Hotels near Central Oakland
- Hotels near Tour-Ed Mine
- Hotels near Carnegie Museum of Art
- Cheap Hotels in Pittsburgh
- Hotels near PNC Park
- Hotels near Phipps Conservatory
- Hotels near PPG Paints Arena
- Hotels near Carnegie Mellon University
- Hotels near South Oakland
- Hotels near Schenley Park
- Hotels near Acrisure Stadium
- Hotels near UPMC Shadyside
- Hotels with Free Airport Shuttle in Pittsburgh
- Hotels near Shadyside
- Hotels near Strip District
- Hotels near Pittsburgh Opera
- Hotels near Gallery G Glass
- Extended Stay America Hotels in Shadyside
- Boutique Hotels in Shadyside
- Extended Stay Hotels in Shadyside
- Marriott Hotels & Resorts in Shadyside
- Luxury Hotels in Shadyside
- Hotel Wedding Venues Hotels in Shadyside
- Resorts & Hotels with Spas in Shadyside
- Hotels with Free Parking in Shadyside
- Hotels with a Swim-up Bar in Shadyside
- 4 Star Hotels in Shadyside
- Hotels with Laundry Facilities in Shadyside
- Cheap Hotels in Shadyside
- 5 Star Hotels in Shadyside
- Hotels with Hot Tubs in Shadyside
- Hotels with Bars in Shadyside
- Romantic Hotels in Shadyside
- Hotels with Fireplaces in Shadyside
- Casino Hotels in Shadyside
- Hotels near Bloomfield
- 4 Star Hotels in Bloomfield
- Extended Stay Hotels in Bloomfield
- Pet-Friendly Hotels in Bloomfield
- Casino Hotels in Bloomfield
- University of Pittsburgh
- University of Pittsburgh Medical Center
- The Nationality Rooms
- Petersen Events Center
- Cathedral of Learning
- Soldiers and Sailors Memorial Hall and Museum
- Carnegie Museum of Natural History
- Heinz Memorial Chapel
- Carnegie Museum of Art
- Phipps Conservatory
- Schenley Park
- Carnegie Mellon University
- Hunt Institute for Botanical Documentation
- Pittsburgh Opera
- Pittsburgh Vacations
- Shadyside Vacations
- Clemente Museum
- Strip District Vacations
- Contemporary Craft
- Market Square
- Visit Pittsburgh
- South Side Vacations
- Ppg Paints Arena
- Temple Sinai
- Senator John Heinz Regional History Centre
- Duquesne University
- Walnut Street
- Western Pennsylvania Sports Museum
- Visit Shadyside
- Roberto Clemente Bridge
- Chatham University
- Visit Bloomfield
- Car rentals near Pittsburgh
- Car rentals near University of Pittsburgh Medical Center
- Luxury Car Rentals near University of Pittsburgh Medical Center
- Car rentals near University of Pittsburgh
- Car rentals near Heinz Memorial Chapel
- Car rentals near Phipps Conservatory
- Car rentals near Carnegie Mellon University
- Premium Car Rentals near Carnegie Mellon University
- Car rentals near UPMC Shadyside
- Car rentals near Shadyside
- Hertz Rental Cars in Shadyside
- Enterprise Rental Cars in Shadyside
- Surprice Car Rentals Rental Cars in Shadyside
- Car rentals near Bloomfield
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.